EP2626355B1 - Verfahren zur Herstellung von Nilotinibhydrochlorid - Google Patents

Verfahren zur Herstellung von Nilotinibhydrochlorid Download PDF

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Publication number
EP2626355B1
EP2626355B1 EP12275010.2A EP12275010A EP2626355B1 EP 2626355 B1 EP2626355 B1 EP 2626355B1 EP 12275010 A EP12275010 A EP 12275010A EP 2626355 B1 EP2626355 B1 EP 2626355B1
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EP
European Patent Office
Prior art keywords
formula
compound
pharmaceutically acceptable
hydrochloride
acceptable salt
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EP12275010.2A
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English (en)
French (fr)
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EP2626355A1 (de
Inventor
Amala Kompella
Adibhatla Kali Satya Bhujanga Rao
Sreenivas Rachakonda
Venugopala Krishna Gampa
Venkaiah Chowdary Nannapaneni
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Natco Pharma Ltd
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Natco Pharma Ltd
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Priority to ES12275010.2T priority Critical patent/ES2564969T3/es
Priority to EP12275010.2A priority patent/EP2626355B1/de
Publication of EP2626355A1 publication Critical patent/EP2626355A1/de
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Definitions

  • pharmaceutically acceptable salt typically refers to a salt prepared from an acid which is acceptable for administration to a patient, such as a mammal. Such salts can be derived from from pharmaceutically acceptable inorganic or organic acids.
  • Salts derived from pharmaceutically acceptable acids include acetic, benzenesulfonic, benzoic, camphosulfonic, citric, ethanesulfonic, formic, fumaric, gluconic, glutamic, hydrobromic, hydrochloric, hydrofluoric, lactic, maleic, malic, mandelic, methanesulfonic, trifluoroacetic, mucic, nitric, pantothenic, phosphoric, succinic, sulfuric, tartaric, p toluenesulfonic, xinafoic (1 hydroxy 2 naphthoic acid), napadisilic (1,5 naphthalenedisulfonic acid), triphenyl acetic and the like.
  • the compound of formula (II) is 4-methyl-3-nitro benzoic acid.
  • the compound of formula (II) is chlorinated, to give the compound of formula (IIA), which is 4-methyl-3-nitro benzoyl chloride:
  • the compound of formula (XI) is 5-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzeneamine and can be obtained by conventional methods known to those skilled in the art.
  • the hydrochloride salt of the compound of formula (I) is in the form of the dihydrate.
  • the crystalline form is thermally stable.
  • the crystalline form is not hygroscopic.
  • the moisture content of the crystalline form after storage for 60 days at 40 °C and 75% relative humidity is less than 10% by weight, more preferably less than 7% by weight, and most preferably less than 6.5% by weight.
  • Nilotinib hydrochloride drug substance from Example 1 and capsules from Example 3 were kept in stability chambers maintained at 40°C / 75% RH and the water contents of the samples were determined by karl-fischer method. The results are set out in Table 5 below.
  • Table 5 Sample Initial moisture Content (%) Final moisture content after 60 days 40°C at humidity of 75% Nilotinib hydrochloride drug stance prepared from example-1 5.26 5.2% Nilotinib hydrochloride capsules prepared from example-3 6.4 6.2%

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (5)

  1. Verfahren zur Herstellung eines Hydrochlorid-Dihydrat-Salzes einer Verbindung der Formel (I):
    Figure imgb0018
     wobei das Verfahren umfasst: das Umwandeln einer Verbindung der Formel (IV):
    Figure imgb0019
     oder eines pharmazeutisch annehmbaren Salzes davon in das Hydrochlorid-Dihydrat-Salz der Verbindung der Formel (I), wobei Salzsäure in einem Methanol-und-Wasser-Medium verwendet wird, um das Hydrochlorid-Dihydrat-Salz zu bilden.
  2. Verfahren nach Anspruch 1, welches umfasst:
    (a) das Umsetzen einer Verbindung der Formel (IV) oder eines pharmazeutisch annehmbaren Salzes davon mit Cyanamid, um eine Verbindung der Formel (V):
    Figure imgb0020
     oder ein pharmazeutisch annehmbares Salz davon zu erhalten;
    (b) das Umsetzen der Verbindung der Formel (V) oder eines pharmazeutisch annehmbaren Salzes davon mit einer Verbindung der Formel (VIII):
    Figure imgb0021
     oder einem pharmazeutisch annehmbaren Salz davon, um die Verbindung der Formel (I) zu erhalten; und
    (c) Das Salifizieren der so erhaltenen Verbindung der Formel (I) mit Salzsäure in einem Methanol-und-Wasser-Medium, um das Hydrochlorid-Dihydrat-Salz zu bilden.
  3. Verfahren nach Anspruch 2, wobei das Verfahren umfasst:
    das Herstellen der Verbindung der Formel (IV) oder eines pharmazeutisch annehmbaren Salzes davon durch Reduzieren der Nitrogruppe einer Verbindung der Formel (III)
    Figure imgb0022
    oder eines pharmazeutisch annehmbaren Salzes davon.
  4. Verfahren nach Anspruch 3, wobei das Verfahren umfasst:
    das Herstellen der Verbindung der Formel (III) oder eines pharmazeutisch annehmbaren Salzes davon durch Umsetzen einer Verbindung der Formel (XI):
    Figure imgb0023
     oder eines pharmazeutisch annehmbaren Salzes davon mit einer Verbindung der Formel (IIA):
    Figure imgb0024
     oder einem pharmazeutisch annehmbaren Salz davon.
  5. Verfahren nach einem der voranstehenden Ansprüche, wobei das Hydrochlorid-Dihydrat-Salz einen Feuchtigkeitsgehalt von 5 Gew.-% bis 7 Gew.-% aufweist.
EP12275010.2A 2012-02-09 2012-02-09 Verfahren zur Herstellung von Nilotinibhydrochlorid Active EP2626355B1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
ES12275010.2T ES2564969T3 (es) 2012-02-09 2012-02-09 Proceso para la preparación de clorhidrato de nilotinib
EP12275010.2A EP2626355B1 (de) 2012-02-09 2012-02-09 Verfahren zur Herstellung von Nilotinibhydrochlorid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP12275010.2A EP2626355B1 (de) 2012-02-09 2012-02-09 Verfahren zur Herstellung von Nilotinibhydrochlorid

Publications (2)

Publication Number Publication Date
EP2626355A1 EP2626355A1 (de) 2013-08-14
EP2626355B1 true EP2626355B1 (de) 2016-02-03

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ES (1) ES2564969T3 (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9636340B2 (en) 2013-11-12 2017-05-02 Ayyappan K. Rajasekaran Kinase inhibitors
EP3404025B1 (de) * 2017-05-16 2019-12-04 F.I.S.- Fabbrica Italiana Sintetici S.p.A. Verfahren zur herstellung von reinem nilotinib und seinen salzen
CN109666023B (zh) * 2017-10-17 2021-03-30 上海复星星泰医药科技有限公司 一种尼洛替尼的制备方法及其中间体
CN111039932B (zh) * 2019-12-13 2023-09-12 安徽峆一药业股份有限公司 一种拉多替尼的高收率合成方法
CN110872279B (zh) * 2019-12-13 2023-09-08 安徽峆一药业股份有限公司 一种尼洛替尼的高收率合成方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0215676D0 (en) 2002-07-05 2002-08-14 Novartis Ag Organic compounds
GT200600315A (es) * 2005-07-20 2007-03-19 Formas cristalinas de 4-metilo-n-[3-(4-metilo-imidazol-1-ilo)-5-trifluorometilo-fenilo]-3-(4-pyridina-3-ilo-pirimidina-2-iloamino)-benzamida
WO2010054056A2 (en) * 2008-11-05 2010-05-14 Teva Pharmaceutical Industries Ltd. Nilotinib hci crystalline forms
WO2010060074A1 (en) * 2008-11-24 2010-05-27 Teva Pharmaceutical Industries Ltd. Preparation of nilotinib and intermediates thereof
KR20130042498A (ko) * 2010-06-21 2013-04-26 테바 파마슈티컬 인더스트리즈 리미티드 닐로티닙 염 및 이의 결정형

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ES2564969T3 (es) 2016-03-30

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